Fluorinated derivatives of meso-(aminophenyl)porphyrins: Synthesis and some transformation

Abstract

Condensation of amino groups in 5-(4-aminophenyl)-10,15,20-triphenylporphyrin and 5,10,15,20-tetrakis(4-aminophenyl)porphyrin with pentafluorobenzaldehyde resulted in corresponding Schiff bases and was shown to be a convenient route for the preparation of fluorinated porphyrin derivatives. Compounds thus obtained were easily transformed into the corresponding amines using sodium borohydride. Fluorinated carboranyl porphyrins were prepared via the nucleophilic substitution of the para-fluorine atom of pentafluorophenyl-substituted amine porphyrin derivatives with carborane S-nucleophiles. The alternative synthetic route to the fluorinated carboranyl porphyrins included the condensation of para-carboranyl-substituted tetrafluorobenzaldehyde with corresponding meso-aminoporphyrins. All prepared porphyrins were characterized by different spectroscopic techniques such as UV-vis, IR, 1H, 11B, 19F NMR and mass spectra.